4-Chloro-3-(trifluoroacetyl)- and 4-chloro-3-(methoxalyl)coumarins as novel and efficient building blocks for the regioselective synthesis of 3,4-fused coumarins / Iaroshenko Viktor O.,Erben Friedrich,Mkrtchyan Satenik,Hakobyan Ani,Vilches-Herrera Marcelo,Dudkin Sergii,Bunescu Alina,Villinger Alexander,Sosnovskikh Vyacheslav Ya,Langer Peter // TETRAHEDRON. - 2011. - V. 67, l. 41. - P. 7946-7955.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

4-Chloro-3-(trifluoroacetyl)- and 4-chloro-3-(methoxalyl)coumarins react with electron-rich aminoheterocycles, dimethyl 1,3-acetonedicarboxylate, hydrazines, alkyl thioglycolates, and methyl sarcosinate to give a variety of 3,4-heteroannulated coumarins. The starting materials were prepared by the reaction of 4-hydroxycoumarin with trifluoroacetic anhydride and methyl 2-chloro-2-oxoacetate in the presence of trimethylsilylchloride. An NMR study and X-ray crystallographic analysis are reported. (C) 2011 Elsevier Ltd. All rights reserved.

Author keywords:

Coumarins; Heterocyclisation; Dinucleophiles; Heterocycles; Regioselectivity NICOTINIC-ACID DERIVATIVES; DIELS-ALDER REACTION; 3-SUBSTITUTED COUMARINS; ACTIVE METHYLENE; FACILE SYNTHESIS; PRIMARY AMINES; RING-CLOSURE; 3-(POLYFLUOROACYL)CHROMONES; CHEMISTRY; ADDUCTS

DOI:

10.1016/j.tet.2011.08.030

Web of Science ID:

ISI:000295564100009

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	OCT 14
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	NICOTINIC-ACID DERIVATIVES; DIELS-ALDER REACTION; 3-SUBSTITUTED COUMARINS; ACTIVE METHYLENE; FACILE SYNTHESIS; PRIMARY AMINES; RING-CLOSURE; 3-(POLYFLUOROACYL)CHROMONES; CHEMISTRY; ADDUCTS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	viktor.iaroshenko@unirostock.de peter.langer@unirostock.de
ORCID-Numbers	Vilches Herrera, Marcelo/0000-0001-8282-8650
Funding-Acknowledgement	DAAD
Funding-Text	Financial support by the DAAD (scholarships for S.M., M.V.-H., and S.D.) is acknowledged.
Number-of-Cited-References	70
Usage-Count-Since-2013	11
Journal-ISO	Tetrahedron
Doc-Delivery-Number	829FN